2-perfluoropentanoylcyclopentanone | 347361-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-perfluoropentanoylcyclopentanone
• 英文别名: 2-(Perfluoropentanoyl)cyclopentanone；2-(2,2,3,3,4,4,5,5,5-nonafluoropentanoyl)cyclopentan-1-one
• CAS: 347361-45-9
• 化学式: C₁₀H₇F₉O₂
• 分子量: 330.15
• InChiKey: PFZDTHHLJUIBOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-perfluoropentanoylcyclopentanone 在 三氟化硼乙醚 、 羟胺 作用下， 以 异丙醇 为溶剂， 反应 15.0h， 以66%的产率得到3a,4,5,6-tetrahydro-3-(nonafluorobutyl)-3H-cyclopenta[c]isoxazol-3-ol
  参考文献：
  名称：

  2-(多氟酰基)环烷酮与羟胺的反应

  摘要：

  The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group. react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(200207)85:7<1960::aid-hlca1960>3.0.co;2-6
• 作为产物：
  描述：

  九氟戊酸甲酯 、 环戊酮 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以71%的产率得到2-perfluoropentanoylcyclopentanone
  参考文献：
  名称：

  来自 2-多氟酰基环烷酮和肼的新型多氟烷基化吡唑：合成和明确的分子结构分配

  摘要：

  2-三氟乙酰环烷酮与甲基肼或苯肼之间的反应仅产生 3-CF3-吡唑。当RFC(O)中多氟取代基的链长...

  DOI：

  10.1139/v01-003

文献信息

• 2,4-Bridged 1,5-bis(fluoroalkyl)-1,3,5-triketones: synthesis and properties
  作者：D.L. Chizhov、K.I. Pashkevich、G.-V. Röschenthaler

  DOI：10.1016/s0022-1139(03)00164-7

  日期：2003.10

  Symmetrical and unsymmetrical bis-fluoroacylcyclopentanones and cyclohexanones were synthesized. NMR data reveal that the keto-enol tautomeric equilibrium is changed markedly by the presence of a trimethylene bridge compared to an ethylene moiety. A considerable influence of the fluoroalkyl chain length was found for 2,6-(bisfluoroacyl)cyclohexanones. (C) 2003 Elsevier B.V. All rights reserved.
• Novel polyfluoroalkylated pyrazoles from 2-polyfluoroacylcycloalkanones and hydrazines: syntheses and unequivocal molecular structure assignment
  作者：D V Sevenard、O G Khomutov、M I Kodess、K I Pashkevich、I Loop、E Lork、G -V Röschenthaler

  DOI：10.1139/v01-003

  日期：2001.2.1

  The reaction between 2-trifluoroacetylcycloalkanones and methylhydrazine or phenylhydrazine exclusively yields 3-CF3-pyrazoles. When the chain length of the polyfluorinated substituent in RFC(O) gr...

  2-三氟乙酰环烷酮与甲基肼或苯肼之间的反应仅产生 3-CF3-吡唑。当RFC(O)中多氟取代基的链长...
• Reaction of 2-(Polyfluoroacyl)cycloalkanones with Hydroxylamine
  作者：Dmitri V. Sevenard、Oleg G. Khomutov、Kazimir I. Pashkevich、Enno Lork、Gerd-Volker Röschenthaler

  DOI：10.1002/1522-2675(200207)85:7<1960::aid-hlca1960>3.0.co;2-6

  日期：2002.7

  The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group. react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis.